Download PDF
Synlett 1991; 1991(11): 841-844
DOI: 10.1055/s-1991-20898
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis and Reactions of a Homochiral Hydroxythiol Derived from Tartaric Acid

Ottorino De Lucchi* , Paola Maglioli, Giovanna Delogu, Giovanni Valle
  • *Dipartimento di Chimica, Università di Sassari, via Vienna 2, I-07100 Sassari, Italy
Further Information

Publication History

Publication Date:
07 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The synthesis of the homochiral, crystalline hydroxythiol 1 (2,3-isopropylidenedioxy-4-mercapto-1,1,4,4-tetraphenyl-1-butanol) from tartaric acid is described. Compound 1 gives with dibromomethane the oxathiepane 3 (5,6-isopropylidenedioxy-4,4,7,7-tetraphenyl-1,3-oxathiepane) which reacts with butyllithium and methyl iodide to afford the 2,2-dimethylated product 7. The lithium derivative of 3 rearranges at temperatures higher than -50 °C to the thiol 8 (3,4-isopropylidenedioxy-6-mercapto-2,2,5, 5-tetraphenyltetrahydropyran). The structures of 7 and 8 were ascertained by X-ray diffraction. The 1,3-oxathiepane 3 was oxidized with total stereoselectively to the single sulfoxide 10. S-methylation of 1 gave 12 which was diastereoselectively oxidized to a single sulfoxide 13.

      >